Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-β-D-glucosamine at the reducing end

Koen M. Halkes, Ted M. Slaghek, Teija K. Hyppönen, Peter H. Kruiskamp, Tomoya Ogawa, Johannis P. Kamerling*, Johannes F.G. Vliegenthart

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

21 Citations (Scopus)

Abstract

To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.

Original languageEnglish
Pages (from-to)161-174
Number of pages14
JournalCarbohydrate Research
Volume309
Issue number2
DOIs
Publication statusPublished - May 1998

Keywords

  • Hyaluronic acid oligosaccharides
  • Hyaluronic acid sulfated analogues
  • Oxidation

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